In Harlem Shuffle: A Novel, two-time Pulitzer Prize-winner Colson Whitehead makes the world from 125th Street and above in New York City as complex a character as the people who inhabit it. He opens his tale in 1959 with a tantalizing line: "His cousin Freddie brought him on the heist one hot night in early June." Freddie is cousin to Ray Carney, who up to now had been "only slightly bent when it came to being crooked." That's what Carney continues to tell himself when Freddie tries to talk him into handling a haul from "the Waldorf of Harlem." Even though Carney thinks, "Robbing the Hotel Theresa was like taking a piss on the Statue of Liberty," he agrees to help Freddie fence the goods from their robbery.
Whitehead suggests that the City itself seems to propel Ray, Freddie, their families, mobsters, the haves and have-nots. Readers watch Harlem change over the course of five years, leading up to the 1964 riots, and the everyday decisions that alter the course of people's lives.